N-Fmoc-L-isoleucine methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Fmoc-L-isoleucine methyl ester
• 英文别名: methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylpentanoate
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: IIDWGJXDOVAEEJ-LGTGAQBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Fmoc-L-isoleucine methyl ester 在 dimethylsulfoxonium methylide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 isoleucine
  参考文献：
  名称：

  甲基亚砜基二甲亚砜是同时脱保护N -Fmoc-α-氨基酸和N -Fmoc-肽酯的氨基和羧基官能团的唯一试剂

  摘要：

  二甲基亚砜基亚甲基被描述为用于同时脱去N -Fmoc-α-氨基酸和N -Fmoc-肽酯的氨基和羧基官能团的独特且有用的试剂。新方法已成功应用于溶液和固相肽合成。所采用的方法也成功地扩展到含有在侧链上带有酸敏感保护基的氨基酸的肽。此外，在N-Fmoc-二肽甲基酯与二甲基亚砜基甲基的脱保护反应中未观察到可测量的差向异构。

  DOI：

  10.1016/j.tet.2012.12.052

文献信息

• Alternative and Chemoselective Deprotection of the ?-Amino and Carboxy Functions ofN-Fmoc-Amino Acid andN-Fmoc-Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N-Dimethylaniline Reagent System
  作者：Maria�Luisa Di Gioia、Antonella Leggio、Adolfo Le Pera、Angelo Liguori、Francesca Perri、Carlo Siciliano

  DOI：10.1002/ejoc.200400321

  日期：2004.11

  The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N-dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• New Strategies for an Efficient Removal of the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group in the Peptide Synthesis
  作者：Antonella Leggio、Angelo Liguori、Anna Napoli、Carlo Siciliano、Giovanni Sindona

  DOI：10.1002/(sici)1099-0690(200002)2000:4<573::aid-ejoc573>3.0.co;2-i

  日期：2000.2

  The aluminium trichloride/toluene system is investigated as a novel, unusual and straightforward reagent for the removal of the 9-fluorenylmethoxycarbonyl (Fmoc) protecting group in the solution peptide synthesis. This procedure avoids any undesired side reactions, such as the frequently observed inversion of the amino acid configuration.

  三氯化铝/甲苯系统被研究为一种新颖、不寻常且直接的试剂，用于去除溶液肽合成中的 9-芴基甲氧基羰基 (Fmoc) 保护基团。该程序避免了任何不需要的副反应，例如经常观察到的氨基酸构型反转。
• AFFINITY FISHING FOR LIGANDS AND PROTEINS RECEPTORS
  申请人：Novo Nordisk A/S

  公开号：EP1588173B1

  公开（公告）日：2008-11-26
• BISUBSTRATE INHIBITORS OF PROTEIN TYROSINE KINASES AS THERAPEUTIC AGENTS
  申请人：Parang Keykavous

  公开号：US20070173437A1

  公开（公告）日：2007-07-26

  A bisubstrate inhibitor of Src kinases, having a nucleotide or N-heteroaromatic moiety; and a peptide/phosphopeptide, peptidomimetic, or phosphopeptide mimic moiety. The moieties are linked by a rigid or a flexible linker. The nucleotide or N-heteroaromatic moiety is ATP, ATP-mimics, N-heteroaromatics including purine-based derivatives, pyrimidine-based derivatives such as 2,4-diamino-5-substituted pyrimidine derivatives, pyrazole[3,4-d]pyrimidine derivatives, pyrrolo[2,3-d]pyrimidine derivatives, pyrido[2,3-d]pyrimidine derivatives, amino-substituted dihydropyrimido[4,5-d]pyrimidinone derivatives, thieno- and furo-substituted derivatives, quinazoline derivatives, and quinoline derivatives, and several natural products such as aminogenistein. The phosphopeptide mimics comprise phosphonate-based phosphotyrosine mimetics such as phosphonomethylphenylalanine (Pmp) and its analogues, carboxylic acid-based phosphotyrosine mimetics such as malonyltyrosine or phenylalanine analogues and their derivatives such as carboxymethyl phenylalanine, uncharged pTyr mimetics, and confonnationally constrained peptides. The phosphopeptide or phosphopeptide mimics inhibits the Src kinases SH2 domain.
• The dimethylsulfoxonium methylide as unique reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-α-amino acid and N-Fmoc-peptide esters
  作者：Mariagiovanna Spinella、Rosaria De Marco、Emilia L. Belsito、Antonella Leggio、Angelo Liguori

  DOI：10.1016/j.tet.2012.12.052

  日期：2013.2

  The dimethylsulfoxonium methylide is described as a unique and useful reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-α-amino acid and N-Fmoc-peptide esters. The new methodology was applied successfully both to solution- and solid-phase peptide synthesis. The adopted methodology was extended successfully also to peptides containing amino acids bearing acid-sensitive

  二甲基亚砜基亚甲基被描述为用于同时脱去N -Fmoc-α-氨基酸和N -Fmoc-肽酯的氨基和羧基官能团的独特且有用的试剂。新方法已成功应用于溶液和固相肽合成。所采用的方法也成功地扩展到含有在侧链上带有酸敏感保护基的氨基酸的肽。此外，在N-Fmoc-二肽甲基酯与二甲基亚砜基甲基的脱保护反应中未观察到可测量的差向异构。